WO2023043039A1 - Nouveau composé pour dispositif électroluminescent, et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé pour dispositif électroluminescent, et dispositif électroluminescent organique le comprenant Download PDF

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WO2023043039A1
WO2023043039A1 PCT/KR2022/010811 KR2022010811W WO2023043039A1 WO 2023043039 A1 WO2023043039 A1 WO 2023043039A1 KR 2022010811 W KR2022010811 W KR 2022010811W WO 2023043039 A1 WO2023043039 A1 WO 2023043039A1
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light emitting
substituted
unsubstituted
emitting device
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Korean (ko)
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함호완
안현철
민병철
김동준
한정우
이형진
안자은
권동열
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주식회사 동진쎄미켐
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Priority claimed from KR1020220017811A external-priority patent/KR20230041942A/ko
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Priority to CN202280062237.5A priority Critical patent/CN117980288A/zh
Publication of WO2023043039A1 publication Critical patent/WO2023043039A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/62—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/30—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages

Definitions

  • the present invention relates to a compound for a light emitting device and an organic light emitting device including the same.
  • Materials used as the organic layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions.
  • the light emitting material is a fluorescent material derived from a singlet excited state of electrons, a phosphorescent material derived from a triplet excited state of electrons, and a delay derived from the movement of electrons from a triplet excited state to a singlet excited state according to a light emitting mechanism. It can be classified as a fluorescent material, and can be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a typical organic light emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode.
  • the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films made of organic compounds.
  • the driving principle of the organic light emitting device having the above structure is as follows.
  • Efficiency of an organic light emitting device can be generally divided into internal light emitting efficiency and external light emitting efficiency.
  • the internal luminous efficiency is related to how efficiently excitons are generated and light conversion is performed in the organic layer interposed between the first electrode and the second electrode, such as the hole transport layer, the light emitting layer, and the electron transport layer.
  • the external luminous efficiency indicates the efficiency in which light generated in the organic layer is extracted to the outside of the organic light emitting device, and it is known that about 20% of the internal luminous efficiency is extracted to the outside.
  • various organic compounds having a refractive index of 1.7 or higher have been applied as a capping layer to prevent total reflection and loss of light going out to the outside.
  • An organic light emitting device including a composite layer structure of a capping layer having a low refractive index and a capping layer having a low refractive index is being developed.
  • LiF has been commercialized as a material for a low refractive index capping layer
  • the problem of high deposition temperature and poor processability of such inorganic compounds has been pointed out, and efforts are being made to replace them with organic compounds.
  • a boron coordination compound is known as a material having a low refractive index, but the boron coordination compound lacks stability, and thus a problem of reducing the lifespan of the organic light emitting device also occurred. Accordingly, efforts are being made to develop an organic capping layer material having excellent compound stability while maintaining a low refractive index.
  • An object of the present invention is to provide a compound for a light emitting device that provides high thermal stability, high efficiency, and long lifespan by linking an amide-based substituent to an adamantane core, and an organic light emitting device including the same.
  • An object of the present invention is to provide a compound for a light emitting device capable of realizing a lower refractive index when applied to a coating layer and an organic light emitting device including the same.
  • a substituent having a low polarization rate may be introduced to have a lower refractive index, it is to provide a compound for a light emitting device that is very effective in improving the efficiency and color purity of an organic light emitting device when applied to a capping layer and an organic light emitting device including the same. The purpose.
  • thermal stability can be improved by including a rigid adamantane linking group, and at the same time, an amide-based substituent is bonded to the adamantane linking group, so it has excellent thin film arrangement, so when applied to the capping layer, external oxygen, air, moisture, etc. It is an object of the present invention to provide a compound for a light emitting device and an organic light emitting device including the same which are more effective in improving the lifespan of the organic light emitting device by improving stability from contamination.
  • An object of the present invention is to provide a compound for a light emitting device capable of realizing an organic light emitting device and an organic light emitting device including the same.
  • a compound for a light emitting device represented by Formula 1 is provided:
  • L1 to L5 are each independently a direct bond, a substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-50 alkenylene group, a substituted or unsubstituted C1-C50 alkyleneoxy group, or an ether group.
  • R and R1 to R11 are each independently hydrogen, heavy hydrogen, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 ⁇ C50 alkyl group, substituted or unsubstituted C2 ⁇ C50 alkenyl group, substituted or unsubstituted C1 ⁇ C50 alkoxy group, substituted or unsubstituted C1 ⁇ C50 sulfide group, substituted or unsubstituted C0 ⁇ C50 silyl group, substituted or unsubstituted C3 ⁇ C50 cycloalkyl group, substituted or unsubstituted C3 ⁇ C50 cycloalkenyl group, substituted or unsubstituted C1 ⁇ C50 heterocyclyl group, substituted or unsubstituted C3 ⁇ C50 aryl group, or substituted or unsubstituted It is a C2 ⁇ C50
  • l is an integer from 0 to 14;
  • n is an integer from 1 to 14;
  • An organic light-emitting device containing the above-described compound for light-emitting devices is provided.
  • an organic light emitting device having high thermal stability, high efficiency, and long lifespan can be realized by having an amide-based substituent connected to an adamantane core.
  • the amide-based substituent has a structure in which a bulky adamantane group is bonded, a low refractive index can be formed, and a particularly wide band gap can be maintained to secure a low attenuation coefficient even in a short wavelength range, which is applied to the capping layer. A lower refractive index can be achieved.
  • thermal stability can be increased by including a rigid adamantane linking group, and at the same time, because it has excellent thin film alignment, stability from contamination by external oxygen, air, moisture, etc. is improved when applied to the capping layer, and thus the organic light emitting device more effective in improving life expectancy.
  • a hole injection layer In addition, it is used in one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an exciton blocking layer, and thus has high color purity, high efficiency, and long lifespan.
  • An organic light emitting device of can be implemented.
  • FIG. 1 is a schematic cross-sectional view showing a configuration of an organic light emitting device according to an exemplary embodiment of the present invention.
  • aryl refers to a C5-50 aromatic hydrocarbon ring group such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenyl It means containing an aromatic ring such as renyl, perylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl, etc., and "heteroaryl” is a C2-50 aromatic ring containing at least one heteroatom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzo furanyl, benzothiophenyl, dibenzothi
  • Ar x (where x is an integer) means a substituted or unsubstituted C6-C50 aryl group or a substituted or unsubstituted C2-C50 heteroaryl group, unless otherwise defined
  • L x (where x is an integer) means a direct bond, a substituted or unsubstituted C6 ⁇ C50 arylene group, or a substituted or unsubstituted C2 ⁇ C50 heteroarylene group, unless otherwise defined
  • R x (where x is An integer) is, unless specifically defined, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1 ⁇ C30 alkyl group, substituted or unsubstituted C2 ⁇ C30 alkenyl group, substituted or unsubstituted C1 ⁇ C30 alkoxy group, substituted or unsubstituted C1 ⁇ C30 sulfide group, substituted or unsub
  • substituted or unsubstituted refers to deuterium, halogen, amino, cyano, nitrile, nitro, nitroso, sulfamoyl, isothiocyanate, thiocyanate groups.
  • An organic light emitting device may include a first electrode, a second electrode, and one or more organic material layers interposed inside the first electrode and the second electrode.
  • the compound for an organic light emitting device of the present invention may be included in any one or more of the organic material layers.
  • An organic light emitting device may be an organic light emitting device including a capping layer. Specifically, a first electrode, a second electrode, one or more organic material layers interposed inside the first electrode and the second electrode, and a capping layer disposed outside any one or more of the first electrode and the second electrode. It may be an organic light emitting device that The compound for an organic light emitting device of the present invention may be included in the capping layer.
  • L1 to L5 are each independently a direct bond, a substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-50 alkenylene group, a substituted or unsubstituted C1-C50 alkyleneoxy group, or an ether group.
  • R and R1 to R11 are each independently hydrogen, heavy hydrogen, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 ⁇ C50 alkyl group, substituted or unsubstituted C2 ⁇ C50 alkenyl group, substituted or unsubstituted C1 ⁇ C50 alkoxy group, substituted or unsubstituted C1 ⁇ C50 sulfide group, substituted or unsubstituted C0 ⁇ C50 silyl group, substituted or unsubstituted C3 ⁇ C50 cycloalkyl group, substituted or unsubstituted C3 ⁇ C50 cycloalkenyl group, substituted or unsubstituted C1 ⁇ C50 heterocyclyl group, substituted or unsubstituted C3 ⁇ C50 aryl group, or substituted or unsubstituted It is a C2 ⁇ C50
  • l is an integer from 0 to 14;
  • n is an integer from 1 to 14;
  • L1 to L5 may each independently be the examples listed above or a combination of three or less of them, specifically substituted or unsubstituted -CH2NR4C(X1)-, substituted or unsubstituted -NR4C( X1)CH2-, substituted or unsubstituted -CH2NR4C(X1)CH2-, substituted or unsubstituted -NR4C(X1)O-, substituted or unsubstituted -ONR4C(X1)-, substituted or unsubstituted -ONR4C (X1)CH2-, substituted or unsubstituted -CH2NR4C(X1)O-, substituted or unsubstituted -ONR4C(X1)O-, substituted or unsubstituted -NR4C(X1)S-, substituted or unsubstituted -SNR4C(X1)-, substituted or unsubstituted -CH2NR4C(X1)S-
  • the compound for a light emitting device of the present invention represented by Chemical Formula 2 or Chemical Formula 3 may have a low refractive index and a low deposition temperature as two amide-based linking groups are directly connected to the adamantane group core.
  • the compound for a light emitting device of the present invention represented by Chemical Formula 4 has a structure in which two amides are bonded to a specific position of an adamantane core, so it has a lower refractive index and at the same time has excellent thermal stability.
  • R1 to R5 may each independently be a substituted or unsubstituted C3-C50 cycloalkyl group or a substituted or unsubstituted C1-C50 heterocyclyl group.
  • R1 to R5 may each independently be a substituted C3-C50 cycloalkyl group or a substituted C1-C50 heterocyclyl group. By having a substituted structure, it can have high thermal stability.
  • R1 to R5 are not limited, but each independently a hydroxyl group, a thiol group, an amino group, a nitrile group, a nitro group, a C1-C30 alkyl group, a C1-C30 halogenated alkyl group, a C1-C30 alkoxy group, a C1 It may be selected from the group consisting of a ⁇ C30 sulfide group, a C0 ⁇ C30 silyl group, a halogen group, a C3 ⁇ C30 cycloalkyl group, a C3 ⁇ C30 cycloalkenyl group, a C1 ⁇ C30 heterocyclyl group, and combinations thereof. . By having such a substituent, it is possible to maintain a low refractive index and have high thermal stability at the same time.
  • R2 and R4 may be hydrogen.
  • R2 and R4 in Formula 2 may be hydrogen
  • R2 and R5 in Formula 3 may be hydrogen.
  • R1 and R3 may not be hydrogen.
  • a lower refractive index can be formed by lowering the intramolecular polarizability and at the same time having a low attenuation coefficient even in a short wavelength range.
  • R1 and R3 may each independently be a substituted or unsubstituted C3-C50 cycloalkyl group or a substituted or unsubstituted C1-C50 heterocyclyl group.
  • R is independently hydrogen, heavy hydrogen, a C1 ⁇ C30 alkyl group, a C1 ⁇ C30 alkoxy group, a C1 ⁇ C30 sulfide group, a C0 ⁇ C30 silyl group, a halogen group, It may be selected from the group consisting of a C3 ⁇ C30 cycloalkyl group, a C1 ⁇ C30 heterocyclyl group, and combinations thereof, and specifically, R may be hydrogen or a C1 ⁇ C10 alkyl group. In this case, a low refractive index can be maintained, and since it is effective in improving thermal stability, the lifetime of the device can be further improved.
  • m in Chemical Formula 1 is specifically an integer of 1 to 4, and may be more specifically 1 or 2. In this case, a low refractive index can be maintained and it can be more effective in improving the deposition temperature.
  • l may be specifically an integer of 0 to 5, and more specifically an integer of 0 to 2.
  • the molecular weight can be minimized, which is effective in improving thermal stability.
  • At least one of -L1-N(-L5R2)-C(X)-L4-R1 and -L2-L3-R3 is each independently selected from the following chemical formulas B-1 to B-46 It can be.
  • W1 is each independently a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, an adamantane group, a dihydroamine group, a dimethylamine group, a hydroxyl group, a methoxy group, a mercaptan group, a methylthio group, and a fluorine group.
  • n is each independently an integer of 0 to 10, specifically an integer of 0 to 4,
  • At least one of -L1-N(-L5R2)-C(X)-L4-R1 and -L2-L3-R3 is each independently selected from the following chemical formulas C-1 to C-14 It can be.
  • -L2-L3-R3 takes a chemical structural formula in which -CO-N-* or -CO-N(CO)-* structure is changed to -N-* in the above chemical structural formulas C-1 to C-14 can
  • the refractive index at a wavelength of 450 nm may have a low refractive index of 1.55 or less.
  • the refractive index at a wavelength of 450 nm may have a low refractive index of 1.50 or less, more specifically 1.45 or less.
  • Formula 1 may be a compound for a light emitting device represented by any one of the following compounds. Since the following compounds are only examples for explaining the present invention, the present invention is not limited thereto.
  • One embodiment of the compound of the present invention can be synthesized by the following schematic reaction scheme.
  • the present invention provides an organic light emitting device containing a compound for a light emitting device.
  • the organic light emitting device includes a first electrode and a second electrode; It includes one or more organic material layers interposed inside the first electrode and the second electrode, and the compound for the light emitting device may be contained in one or more of the organic material layers.
  • the organic material layer containing the compound for the light emitting device may be at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an exciton blocking layer. there is. Specifically, it may be a hole transport layer, a light emitting auxiliary layer, or a light emitting layer.
  • the compound for a light emitting device of the present invention may be used alone or in combination with a known organic light emitting compound.
  • the light emitting auxiliary layer is a layer formed between the hole transport layer and the light emitting layer, and may be referred to as a second hole transport layer or a third hole transport layer according to the number of hole transport layers.
  • the organic light emitting device includes a first electrode and a second electrode; one or more organic material layers interposed inside the first electrode and the second electrode; A capping layer disposed outside any one or more of the first electrode and the second electrode may be further included, and the compound for the light emitting device may be included in the capping layer.
  • the organic light emitting device may include a first electrode, a second electrode, one or more organic material layers interposed inside the first electrode and the second electrode, and a capping layer, wherein the The capping layer may be disposed on an outer side of at least one of the first electrode and the second electrode.
  • a side adjacent to the organic material layer interposed between the first electrode and the second electrode is referred to as an inner side
  • a side not adjacent to the organic material layer is referred to as an outer side. That is, when the capping layer is disposed outside the first electrode, the first electrode is interposed between the capping layer and the organic layer, and when the capping layer is disposed outside the second electrode, the second electrode is interposed between the capping layer and the organic layer. do.
  • one or more layers of various organic materials may be interposed inside the first electrode and the second electrode, and the outer side of any one or more of the first electrode and the second electrode.
  • a capping layer may be formed on. That is, the capping layer may be formed on both the outside of the first electrode and the outside of the second electrode, or may be formed only on the outside of the first electrode or the outside of the second electrode.
  • the capping layer may include the compound for a light emitting device according to the present invention, and may include the compound for a light emitting device according to the present invention alone, two or more types, or a known compound together.
  • the capping layer may have a thickness of 100 ⁇ to 3000 ⁇ .
  • the capping layer may have a composite capping layer structure in which a first capping layer having a relatively low refractive index and a second capping layer having a higher refractive index than the first capping layer are stacked.
  • the device compound may be included in the first capping layer.
  • the stacking order of the first capping layer and the second capping layer is not limited, and the first capping layer may be disposed outside the second capping layer, or conversely, the second capping layer may be disposed outside the first capping layer.
  • the second capping layer may be interposed between the first capping layer and the first electrode or the second electrode, and specifically, the second capping layer includes the first capping layer and the first electrode. Alternatively, it may have a structure in contact with the first capping layer and the second electrode.
  • first capping layer and the second capping layer may be alternately stacked, and the stacking order is not limited as described above, and the first capping layer may be disposed outside the second capping layer, and vice versa.
  • the second capping layer may be disposed outside the first capping layer.
  • the first capping layer may have a refractive index of 1.55 or less, specifically 1.50 or less, more specifically 1.45 or less at a wavelength of 450 nm.
  • the second capping layer may have a refractive index of 2.10 or more, specifically 2.25 or more, and more specifically 2.30 or more at a wavelength of 450 nm, and the difference between the refractive index of the first capping layer and the second capping layer at a wavelength of 450 nm is 0.2 to 1.2 range, more specifically within the range of 0.4 to 1.2.
  • the difference in refractive index is less than 0.2 or greater than 1.2, there is a problem in that light extraction efficiency is lowered.
  • the total thickness of the first capping layer may be in the range of 50 ⁇ to 2000 ⁇ , and the total thickness of the second capping layer may be in the range of 50 ⁇ to 2000 ⁇ .
  • the capping layer may have a refractive index gradient.
  • the refractive index may gradually decrease toward the outside, and the refractive index may gradually increase toward the outside.
  • a refractive index gradient may be implemented in the capping layer by forming a capping layer by gradually varying the concentration of the compound for a light emitting device according to the present invention.
  • the organic material layer may generally include a hole transport layer, a light emitting layer, and an electron transport layer constituting the light emitting unit, but may not be limited thereto.
  • the organic light emitting device includes a hole injection layer (HIL), a hole transport layer (HTL), and a light emitting layer ( EML), an electron transport layer (ETL), and an electron injection layer (EIL) may include one or more organic material layers constituting the light emitting part.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron transport layer
  • EIL electron injection layer
  • ETL electron transport layer
  • EIL electron injection layer
  • a hole blocking layer (HBL, not shown) or an electron transport auxiliary layer is formed between the light emitting layer (EML) and the electron transport layer (ETL)
  • EBL electron blocking layer
  • EBL electron blocking layer
  • FIG. 1 is a cross-sectional view schematically showing the configuration of an organic light emitting device according to an embodiment of the present invention.
  • An organic light emitting device according to an embodiment of the present invention may be manufactured as the structure described in FIG. 1 .
  • the organic light emitting device includes a substrate 100, a first electrode 1000, a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, and an electron injection layer from below. 600, the second electrode 2000, and the capping layer 3000 may be sequentially stacked.
  • the capping layer 3000 may have a structure in which a first capping layer and a second capping layer are stacked as described above.
  • a third capping layer having a different refractive index from the first capping layer and the second capping layer may be further added to have a stacked structure, but is not limited thereto.
  • the capping layer may have a refractive index gradient. In the refractive index gradient, the refractive index may gradually decrease toward the outside, and the refractive index may gradually increase toward the outside.
  • the substrate 100 may use a substrate generally used in an organic light emitting device, and in particular, a transparent glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, or a flexible plastic substrate.
  • a transparent glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance
  • a flexible plastic substrate can be
  • the first electrode 1000 is used as a hole injection electrode for hole injection of an organic light emitting device.
  • the first electrode 1000 is manufactured using a material having a low work function to enable injection of holes, and is formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene. It can be.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • graphene graphene
  • the hole injection layer 200 is formed by depositing a hole injection layer material on top of the first electrode 1000 by a method such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, and the like It can be.
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the desired structure and thermal characteristics of the hole injection layer 200, etc. In general, a deposition temperature of 50 to 500° C., a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 ⁇ /sec, and a layer thickness of 10 ⁇ to 5 ⁇ m can be appropriately selected.
  • a charge generation layer may be additionally deposited on the surface of the hole injection layer 200 if necessary. Conventional materials can be used as the material for the charge generation layer, and HATCN is exemplified.
  • the hole transport layer 300 may be formed by depositing a hole transport layer material on top of the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method.
  • a vacuum deposition method the deposition conditions vary depending on the compound used, but are generally selected within the same range of conditions as those for forming the hole injection layer 200.
  • the hole transport layer 300 may be formed using a known compound.
  • the hole transport layer 300 may have one or more layers, and although not shown in FIG. 1 , it may include two layers of a first hole transport layer and a second hole transport layer (emission auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include the compound for a light emitting device according to the present invention.
  • the light emitting layer 400 may be formed by depositing a light emitting layer material on top of the hole transport layer 300 or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method.
  • a vacuum deposition method the deposition conditions vary depending on the compound used, but are generally selected within the same range of conditions as those for forming the hole injection layer 200.
  • the light emitting layer material may use a compound for a light emitting device according to the present invention or a known compound as a host or dopant.
  • a compound for a light emitting device may be used as a host and a known compound may be used as a dopant.
  • the dopant is not limited, but a phosphorescent or fluorescent dopant may be used together to form the light emitting layer.
  • BD142 N6,N12-bis(3,4-dimethylphenyl)-N6,N12-dimethylchrysene-6,12-diamine
  • green phosphorescence as a phosphorescent dopant.
  • Dopant Ir(ppy)3 tris(2-phenylpyridine)iridium
  • UDC's red phosphorescent dopant RD61, etc. can be co-vacuum deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but is preferably doped with 0.01 to 15 parts by weight of the dopant based on 100 parts by weight of the host.
  • the content of the dopant is less than 0.01 parts by weight, there is a problem that the dopant amount is not sufficient and the color development is not performed properly, and if it exceeds 15 parts by weight, there is a problem that the efficiency is rapidly reduced due to the concentration quenching phenomenon.
  • a hole blocking material is added to the top of the light emitting layer 400 to prevent triplet excitons or holes from diffusing into the electron transport layer 500 by vacuum deposition method or It can be laminated through a spin coating method.
  • the hole blocking material that can be used is not particularly limited, and known materials can be arbitrarily selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open No.
  • the light emitting layer 400 of the present invention may include one or more blue light emitting layers or two or more layers.
  • the electron transport layer 500 is formed on the light emitting layer 400, and may be formed by a method such as a vacuum deposition method, a spin coating method, or a cast method.
  • the deposition conditions of the electron transport layer 500 vary depending on the compound used, but it is generally preferable to select them within the same range of conditions as those for forming the hole injection layer 200 .
  • a compound for a light emitting device according to the present invention or a conventionally known material may be arbitrarily selected and used.
  • quinoline derivatives particularly tris(8-quinolinolato)aluminum (Alq3), or ET4(6,6'-(3,4-dimethyl-1,1- dimethyl-1H-silol-2,5-diyl)di-2,2′-bipyridine) can be used.
  • the electron injection layer 600 may be formed by depositing an electron injection layer material on top of the electron transport layer 500, and may be formed by a method such as a vacuum deposition method, a spin coating method, or a cast method.
  • a method such as a vacuum deposition method, a spin coating method, or a cast method.
  • a compound for a light emitting device according to the present invention or a known material such as LiF, NaCl, CsF, LiO, or BaO may be used.
  • the second electrode 2000 is used as an electron injection electrode, and may be formed on top of the electron injection layer 600 by a vacuum deposition method or a sputtering method.
  • Various metals may be used as the material of the second electrode 2000 . Specific examples include lithium (Li), aluminum (Al), gold (Au), silver (Ag), magnesium (Mg), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), There is a material such as magnesium-silver (Mg-Ag), but is not limited thereto.
  • a transmissive electron injection electrode using ITO or IZO may be used to obtain a top light emitting device.
  • the organic light emitting device of the present invention includes the first electrode 1000, the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, and the second electrode described above.
  • organic light emitting diodes having a structure including (2000) and a capping layer 3000 organic light emitting diodes having various structures are possible, and one or two intermediate layers may be additionally included as needed.
  • each organic material layer formed according to the present invention may be adjusted according to a required degree, specifically 1 to 1,000 nm, and more specifically 1 to 150 nm.
  • the capping layer 3000 may be formed on an outer surface on which the hole injection layer 200 is not formed among both side surfaces of the first electrode 1000 .
  • the electron injection layer 600 may be formed on the outer side of both sides of the second electrode 2000 on which the electron injection layer 600 is not formed, but is not limited thereto.
  • the capping layer 3000 may be formed through a deposition process, and may have a thickness of 100 to 3,000 ⁇ , more specifically, 300 to 2,000 ⁇ . Through such thickness control, it is possible to prevent the transmittance of the capping layer 3000 from being lowered.
  • an organic material layer may be additionally formed.
  • an organic material layer having various functions may be additionally formed on the top (outer surface) of the capping layer 3000, and one or more separate functional layers may be inserted and present in the middle of the capping layer 3000. It is not.
  • the present invention is manufactured to have the structure of the organic light emitting device shown in FIG. 1 as an example.
  • the manufactured organic light emitting device includes an anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection layer 600 from below. ) / cathode (electron injection electrode 2000) / capping layer 3000 are stacked in this order.
  • the capping layer 3000 may have a multilayer structure in which the first capping layer and the second capping layer are combined.
  • the substrate 10 may be a transparent glass substrate or a flexible plastic substrate.
  • the hole injection electrode 1000 is used as an anode for hole injection of an organic light emitting device.
  • a material having a low work function is used to enable injection of holes, and it may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • graphene graphene
  • the materials listed in Table 3 were used for the hole injection layer 200, the charge generation layer, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, and the high refractive index capping layer.
  • a cathode 2000 for electron injection was formed on the electron injection layer 600 .
  • Various metals can be used as the cathode. Specific examples include materials such as aluminum, gold, silver, magnesium, and a magnesium-silver alloy.
  • ITO indium tin oxide
  • a reflective layer containing silver (Ag) was formed was cleaned with ultrasonic waves in distilled water. After washing with distilled water, ultrasonic cleaning was performed using solvents such as isopropyl alcohol, acetone, and methanol, and drying was performed. Thereafter, 100 ⁇ of HT01 and NDP9 were doped with 3% by weight of NDP9 as a hole injection layer on the ITO substrate, and 1000 ⁇ of HT01 as a hole transport layer were deposited, respectively. ⁇ thickness was deposited.
  • an electron transport layer a mixture of ET01 and Liq (1:1, wt./wt.) was deposited to a thickness of 300 ⁇ , and then LiF was deposited to a thickness of 10 ⁇ to form an electron injection layer.
  • MgAg was deposited to a thickness of 15 nm to form a cathode
  • CPM01 was deposited to a thickness of 950 ⁇ as a high refractive capping layer on the cathode
  • the compound prepared in Synthesis Example 1 was deposited to a thickness of 400 ⁇ as a low refractive capping layer.
  • An organic light emitting device was manufactured by encapsulating the device in a glove box.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, but formed with a low refractive index capping layer using the compounds prepared in Synthesis Example 2 to Synthesis Example 21, respectively.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, but using Comparative Compounds 1 to 4 shown in Table 4 below, respectively, to form a low refractive index capping layer.
  • the present invention can have a low refractive index by being connected through a bulky adamantane core and have a lower refractive index by connecting two or more amine-based substituents with low polarizability.
  • the compounds according to the present invention exhibit a low refractive index of 1.50 or less, specifically 1.45 or less, at a wavelength of 450 nm.
  • other compounds according to the present invention also showed a low refractive index of 1.55 or less, specifically 1.50 or less, and more specifically 1.45 or less at a wavelength of 450 nm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé pour un dispositif électroluminescent, et un dispositif électroluminescent organique le comprenant.
PCT/KR2022/010811 2021-09-17 2022-07-22 Nouveau composé pour dispositif électroluminescent, et dispositif électroluminescent organique le comprenant WO2023043039A1 (fr)

Priority Applications (1)

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CN202280062237.5A CN117980288A (zh) 2021-09-17 2022-07-22 新型的发光元件用化合物以及包含其的有机发光元件

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KR20210124580 2021-09-17
KR10-2021-0124580 2021-09-17
KR1020220017811A KR20230041942A (ko) 2021-09-17 2022-02-10 신규한 발광 소자용 화합물 및 이를 포함하는 유기 발광 소자
KR10-2022-0017811 2022-02-10

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11329734A (ja) 1998-03-10 1999-11-30 Mitsubishi Chemical Corp 有機電界発光素子
KR20110036797A (ko) * 2008-07-25 2011-04-11 하. 룬트벡 아크티에 셀스카브 아다만틸 디아미드 유도체 및 이의 용도
WO2012088316A1 (fr) * 2010-12-22 2012-06-28 Georgia Tech Research Corporation Hôtes de 2-alkyl-5-phényl-oxadiazole-carbazole pour émetteurs hébergés
WO2014168138A1 (fr) * 2013-04-11 2014-10-16 新日鉄住金化学株式会社 Composé adamantane pour éléments électroluminescents organiques, et élément électroluminescent organique
KR102210267B1 (ko) * 2020-05-26 2021-02-01 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20210024969A (ko) * 2019-08-26 2021-03-08 주식회사 동진쎄미켐 캡핑층을 포함하는 유기 발광 소자 및 이에 적용되는 캡핑층용 화합물

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11329734A (ja) 1998-03-10 1999-11-30 Mitsubishi Chemical Corp 有機電界発光素子
KR20110036797A (ko) * 2008-07-25 2011-04-11 하. 룬트벡 아크티에 셀스카브 아다만틸 디아미드 유도체 및 이의 용도
WO2012088316A1 (fr) * 2010-12-22 2012-06-28 Georgia Tech Research Corporation Hôtes de 2-alkyl-5-phényl-oxadiazole-carbazole pour émetteurs hébergés
WO2014168138A1 (fr) * 2013-04-11 2014-10-16 新日鉄住金化学株式会社 Composé adamantane pour éléments électroluminescents organiques, et élément électroluminescent organique
KR20210024969A (ko) * 2019-08-26 2021-03-08 주식회사 동진쎄미켐 캡핑층을 포함하는 유기 발광 소자 및 이에 적용되는 캡핑층용 화합물
KR102210267B1 (ko) * 2020-05-26 2021-02-01 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자

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